Sodium borohydride → {6-[4-(Trifluoromethoxy)phenyl]pyridin-3-yl}methanol

HRID 1242305Notes

Reaction equation

HRID 1242305 reaction equation
[F:1][C:2]([F:19])([F:18])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:15]=[CH:14][C:13]([CH:16]=[O:17])=[CH:12][CH:11]=2)=[CH:6][CH:5]=1.[BH4-].[Na+]>CCO>[F:19][C:2]([F:1])([F:18])[O:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[N:15]=[CH:14][C:13]([CH2:16][OH:17])=[CH:12][CH:11]=2)=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 219356276-[4-(Trifluoromethoxy)phenyl]-3-pyridinecarboxaldehyde

Product 1

HCID 21935933{6-[4-(Trifluoromethoxy)phenyl]pyridin-3-yl}methanol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2.00 g (7.48 mmol) of commercially available 6-(4-trifluoromethoxy-phenyl)-pyridine-3-carbaldehyde was dissolved in 37 ml of EtOH and treated at 0° C. with 0.283 g (7.48 mmol) of NaBH4. After 10 Min. the cooling bath was removed and stirring continued at ambient temperature. Pouring onto crashed ice, twofold extraction with AcOEt, washing with water, drying over sodium sulfate, and evaporation of the solvents afforded 2.08 g of pure title compound as off-white solid of mp. 57–58° C.

Workup

  1. customthe cooling bath was removed
  2. customcontinued at ambient temperature
  3. additionPouring
  4. extractionice, twofold extraction with AcOEt
  5. washwashing with water
  6. dry with materialdrying over sodium sulfate, and evaporation of the solvents

Sources & evidence

ORD record
ord-e7a0896eb32c48dabd40056b2f32ed17
Source dataset
uspto-grants-2006_10
Patent number
US07115611B2

Reaction notes

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